This question is similar to that stated in Conformal Welding Reference:
Let $\Sigma$ be a 1-dim compact connected complex manifold with boundary $\partial \Sigma= \partial\Sigma^+ \cup \partial\Sigma^-$, s.t. for every $X \in \pi_0(\partial \Sigma^+)\, (X \in \pi_0(\partial \Sigma^-))$ there is an orientation preserving (reversing) diffeomorphism $\varphi_X: \mathbb{S}^1 \to X$, s.t. $\varphi_X$ extends to a homeomorphism $\hat{\varphi}_{X,r}: \mathbb A_r \to U_{X,r}$ from the half open annuli, bounded by circles with radius $1$ and $r \neq 1$, to an open nbhd $U_{X,r}$ of $X$.
My question is: Which (minimal) additional structure (like complex/real analiticity, etc) should $\hat{\varphi}_{X,r}|_{\text{int}(\mathbb A_r)}$ possess, to make the following possible?
For two such tuples $(\Sigma, \{\varphi_X\}_{X \in \pi_0(\partial \Sigma)})$, $(\Sigma', \{\psi_Y\}_{Y \in \pi_0(\partial \Sigma')})$ I'd like to glue $\Sigma$ and $\Sigma'$ at $X \in \pi_0(\partial \Sigma^+)$ and $Y \in \pi_0(\partial \Sigma'^-)$, such that there exists a unique compatible holomorphic structure on the quotient $\Sigma \amalg \Sigma'/\sim$ with identification coming from $\hat{\varphi}_{X,r}\circ \text{inv}_{\mathbb{C}}\circ\hat{\psi}_{Y,r'}^{-1}$ restricted to $\hat{\psi}_{Y,r'}(\mathbb{A}_{r'} \cap \mathbb{A}_{\frac{1}{r}})$. This should not depend on $r$ and $r'$ up to isomorphism.
EDIT: Question 2: This question is a little more qualitative.. If I drop the extension and assume $\varphi_X$ to be real analytic, then identifying the boundaries should provide a new Riemann surface with unique complex structure, since real analytic maps extend to complex analytic ones uniquely. Why do some people (Neretin, Huang, etc) require extensions of these boundary parametrizations when defining the moduli of Riemann surfaces with parametrized boundaries?